Ethyl Acetate → HCID 57382977, compound

HRID 2168250Notes

Reaction equation

HRID 2168250 reaction equation
Cl[C:2]1[C:3]2[C:10]([CH3:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:12][O:13][CH2:14][CH:15]1[CH:20]([NH:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18][NH:17][CH2:16]1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CN1C(=O)CCC1>[CH3:12][O:13][CH2:14][CH:15]1[CH:20]([NH:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18][N:17]([C:2]2[C:3]3[C:10]([CH3:11])=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:16]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 67988153HCID 67988153, compound

Product 1

HCID 57382977HCID 57382977, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine D4 (218 mg), N-{3-[(methyloxy)methyl]-4-piperidinyl}benzamide D35 (500 mg) and N,N-diisopropylethylamine (504 mg, 3.9 mmol) were dissolved in NMP (10 ml). The tube was sealed and the reaction carried out in the microwave. The reaction was heated at 150° C. for 3 hours. The reaction mixture was poured into ethyl acetate (120 ml), washed with water (3×30 ml), brine (2×30 ml). Organic layer collected and dried with MgSO4, filtered and solvent removed. Purification of the crude product by chromatography on silica gel eluting with DCM/MeOH 30/1 to give product. Repurified by prep-HPLC (column: x-bridge C18sun, 30×, 50 mm; mobile phase: A 10 mmol/L NH3.H2O B ACN; gradient: 35-40% ACN in 6-7 min. Rt 6.3 min to give the product E42 as a yellow solid in 86 mg. LCMS [M+H] [email protected] min (mixture of 2 isomers) (5 min run)

Workup

  1. customThe tube was sealed
  2. washwashed with water (3×30 ml), brine (2×30 ml)
  3. customOrganic layer collected
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customsolvent removed
  7. customPurification of the crude product by chromatography on silica gel eluting with DCM/MeOH 30/1
  8. customto give product
  9. customRepurified by prep-HPLC (column
  10. customRt 6.3 min to give the product E42 as a yellow solid in 86 mg
  11. additionLCMS [M+H] [email protected] min (mixture of 2 isomers) (5 min run)

Sources & evidence

ORD record
ord-772a27c4076d4ce195d0eee9fb09ab5f
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

Loading…